When the Life You Choose Is a Life Less Ordinary

Next week, I’ll take an hour-and-a-half train ride along the Hudson River to upstate New York to spend Christmas with my conservative Catholic family. Dinner will be riddled with the same questions I’ve been getting asked for the past decade: “Do you have a boyfriend?” “Has he popped the question?” “Did you get a real job?” Each year it gets harder to brush them off. When we’re young, it feels romantic and exciting to live a life that’s unique or subversive, but as we get older, fear of future discomfort or alienation pushes many people to make more conventional, “safe” choices. But what if you never want to give up the dream?

Let me provide some context. In the past year, I’ve been invited to almost as many weddings and baby showers as I have birthday parties. I’m 28, and suddenly the people around me—both new friends and old—are doing the things people do: growing up, starting families, getting promotions, and hitting those conventional milestones that validate us as real, valuable, mature human beings. But what if you don’t fit that conventional mold? What if you’re me: a self-employed college dropout with three roommates and no health insurance, experimenting with some late-onset lesbianism? I understand that much of my adult life has not been “by the book.” Still, the realization that I won’t be hitting any of adulthood’s life-affirming markers anytime soon, or perhaps ever, has left me slightly unnerved.

I diverted from the standard path at seventeen, when I made the impulsive decision to move to England to study acting, only to drop out six months later because I cared more about partying than my studies. After moving into a squatted artist commune, I started dressing like Courtney Love on a bad day. Around 21, my life started to take some structure. I interned at a series of magazines, which sparked an interest in writing, after which I wrote articles for free or almost nothing while working crappy side jobs. I started a sex blog (to my Catholic parents’ despair) that ended up becoming something people liked. I moved to New York at 25 with no money, lived in some seriously sketchy apartments, and assisted a dominatrix to earn extra cash while trying to make it work as a writer.

Eventually, I got to a place where I am proud of what I’ve become. I like that I live on my own schedule and that I can write this article from my bed, in my pajamas, with my laptop resting on my chest. It feels affirming to have an audience for whom my writing means something. Still, I don’t have a home I call my own; I don’t have a sparkly diamond on my hand; and although I’ve been told since I was young that one day the biological baby urge would just suddenly hit, the fact that I’m approaching 30 and I haven’t even experienced the slightest tremor has left me thinking that it might never happen for me.

But the truth is that my alternative life choices still upset my parents. And that still upsets me. I can’t share my successes with my dad, who sees only shame in writing about sex and sexuality. My brother gets to bring his girlfriend to Christmas, but I can’t bring mine, because that would destroy everyone’s delusion that she doesn’t exist. I spend so much time feeling anxious and insecure, with no way to gauge whether the work I am doing will result in any lucrative or emotional gain later in life. Going your own way, I was finding, can be rewarding, but also incredibly disorienting.

This time around, to help ease my pre-holiday anxieties, I decided to talk to my mom. Her milestones won’t be mine, but I was still interested in learning about her life decisions. She and my dad were high-school sweethearts, they got married in a church, had two babies, and today they’re still happily together, living and working in the same town they grew up in. She agreed to do this interview even though she probably won’t read the resulting article. She generally avoids looking at anything I create (“for her own health,” she says), which is actually probably why we’ve been able to sustain such a close relationship.

“I think it’s a natural impulse to look back and wonder, What if . . . ?” she told me over the phone last week. She said she often wonders what her life would have been like if she went away to college. But she also understands that if she had, she probably wouldn’t have married my dad, and therefore wouldn’t have the life she loves now. My mom told me, “If you’re happy in the present, the past seems perfectly designed—both the good and the bad—because you know if just one thing was different, you wouldn’t be where you are. But if you’re unhappy in the present, you can’t help but look back and try to pinpoint all the bad decisions you made, all the things you could have done better.”

My mom wasn’t sure the conventional route was right for her, but she took a leap of faith, and it worked out. She said, “Maybe it’s because I’m someone who’s happier with a simpler life, but in my opinion, I made the right choices for myself.” Still, she admitted that at rocky emotional points, she regretted not being more ambitious in her career: “If your family is what makes you feel fulfilled, when things at home get dysfunctional, you feel like a failure. You think, I don’t even have a high-powered job and I can’t even keep my family life in sync.”

Our conversation reminded me of a famous quote that is often attributed to Mark Twain, but is actually from a book you’ve never heard of called P.S. I Love You by H. Jackson Brown, Jr., which goes like this:

Twenty years from now, you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.

Even though I’m totally on the same page, I still understand that conventional behaviors like starting a family or buying a house or getting a full-time job are satisfying, and help to chart one’s progress in the world. They exist because they fulfill basic human necessities: People don’t want to be alone; we want to be part of a community, we want to feel appreciated and secure. And I can’t dismiss these huge life steps—like having a child—just because they feel conventional to me. But what I’m learning is that maybe there are other, less traditional ways to tick off those boxes. Maybe those of us living outside the lines have to create our own milestones—you make your first movie, you get an apartment with your girlfriend, you sell a painting, you run a marathon, you redecorate your house, you go traveling. Maybe you’re a queer kid born to religious parents, so you form a core group of close friends who become your surrogate family. Maybe you’re someone who creates something—be it art, words, ideas, clothing, furniture, whatever—and for you, that fulfills the same basic need to leave a legacy that having a baby does for others.

So what I’ll be reminding myself next week while home for the holidays is this: Even in a nonconventional life, you have to have your own road signs, but you may have to make them yourself. Otherwise, you’re treading water. And at this time of the year, with the holidays, there is this real sense of time passing. We all evaluate ourselves; we all hope on some level that at the end of the year, we’re better than the last. So sure, I can throw off the bowlines, but if it’s not the lighthouse that guides me, then maybe it’s the moon and the stars. Be confident enough to assess your own progress. If you choose to live alternatively, then you should embrace that and do the best you can rather than waste your time thinking about how much more comfortable the grass looks on the other side. For me, uncertainty feels like a small price to pay to live a life less calculated.